The Prisoners are pirates who are locked up in the jail of Tortooga. In order to free the imprisoned pirates (one of which must be freed to progress), Mickey must find a trio of keys throughout the area. The keys can be found in the following areas:
- A platform underneath a thinnable ramp that leads up to the second floor of the main section of Tortooga contains a key. After getting the key you can paint in a portion of the waterwheel to head back up.
- The chimney directly above the jail is thinnable and contains a key.
- The very top of the tallest building in Tortooga is thinnable and contains a key.
The pirate on the right will ask you to find several lamp stands located in the area to raise the supposed remnants of an old ride in the harbor area and thus assigns you the optional Paint the Lanterns quest. After painting in all 3 lanterns, several platforms and a Treasure Chest containing with a pin.
The pirate in the middle will unlock access to the bottom of the well and assign Mickey the optional Bottom of the Well quest. When you go to the bottom of the well and spin the gear, a platform will rise up out of the Thinner right outside which you can jump to and holds yet another chest (the chest is thinned out this time) containing a pin.
It's more so recommended that Mickey frees the pirate on the left however as he'll open the door to the area with Beluga Billy's belongings. Any pirates who are not freed are later revealed to have been kidnapped by the beetleworx pirates .